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Total synthesis of Deoxy-Estrone:
Reference: Nicolaou, K. C.; Barnette, W. E. Chem. Commun 1979, 1119. DOI
Keywords: Ketone → Ketal • CarboxEster → Alkyl-OH • O-H → O-SO2R • Ketal → Ketone • ConjAdd-Alkylation • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Cu-Vinyl+Enone • Enone+Cu-Vinyl • Alkyl-X+Enolate • ConjAdd Cu-R • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Chelotropic, SO2 • Diels-Alder, Intram, o-Xylylene • Steroid synthesis •
Reagents: Vinyl-MgX • CuI • Bromoacetate • Glycol • TsOH • AlH4-Li+ • TsCl, Py • LiCHR-Sulfonyl • KH • Acetic acid • SO2

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